We explore the relationships between gender, career ambition, and the emergence of executive leadership. Growing research in public administration shows that career systems shape bureaucrats’ ambitions, political behavior, and management. Yet career systems are not neutral conduits of talent: Administrators are more likely to pursue advancement when career systems favor them. This study proposes that women and men respond to gendered public career systems. Using national- and state-level data on public school managers in the United States, we find gender disparities in the career paths that lead educators from the classroom to the superintendent’s suite. Specifically, we find that female and elementary school teachers advance more slowly than male and secondary school teachers. We also find gender disparities in certification and experience among principals. Accordingly, female and elementary principals report lower levels of ambition. Such gendered career systems may lead to biases in policy agendas and public management.